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Related Concept Videos

Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility02:34

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Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, and solubilities (miscibilities) of substances. Molar mass, molecular shape, and polarity affect the strength of different intermolecular forces, which influence the magnitude of physical properties across a family of molecules.
Temporary attractive forces like dispersion are present in all molecules, whether they are polar or nonpolar. They...
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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Physical Properties of Alkanes02:33

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Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...
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Halogenation of Alkenes02:46

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
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Structure-melting relations in isomeric dibromobenzenes.

Kamil F Dziubek1, Andrzej Katrusiak1

  • 1Faculty of Chemistry, Adam Mickiewicz University, ul. Umultowska 89b, Poznań 61-614, Poland.

Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
|June 4, 2014
PubMed
Summary

The melting points of dibromobenzene isomers are linked to their molecular symmetry and crystal packing. Higher symmetry in 1,4-dibromobenzene leads to a higher melting point compared to less symmetrical isomers.

Keywords:
halogen...halogen interactionshigh pressurestructure–property relationships

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Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Physical organic chemistry

Background:

  • Melting points of isomers often vary due to differences in molecular symmetry and crystal packing.
  • Carnelley's rule relates molecular symmetry to melting point, with higher symmetry generally leading to higher melting points.
  • Halogen bonding interactions can influence crystal lattice stability and melting behavior.

Purpose of the Study:

  • To investigate the crystal structures of 1,2- and 1,3-dibromobenzene isomers.
  • To correlate the observed crystal structures and molecular symmetry with their respective melting points.
  • To compare the structural and thermal properties of dibromobenzene isomers with dichlorobenzene isomers.

Main Methods:

  • In situ X-ray diffraction studies under high pressure (diamond-anvil cell) and isobaric conditions (glass capillary).
  • Crystal structure determination for 1,2- and 1,3-dibromobenzene at various pressures and temperatures.
  • Analysis of crystal packing, molecular symmetry, and potential intermolecular interactions (e.g., halogen bonds).

Main Results:

  • 1,2-dibromobenzene crystallizes in an orthorhombic system (space group Pbca, Z'=1) at 0.2 GPa and 295 K.
  • 1,3-dibromobenzene crystallizes in an orthorhombic system (space group P212121, Z'=2) at 0.3 GPa and 295 K.
  • 1,4-dibromobenzene crystallizes as monoclinic (space group P21/a) and has a significantly higher melting point, consistent with its higher molecular symmetry and efficient packing.

Conclusions:

  • The distinct melting points of dibromobenzene isomers are directly related to their molecular symmetry and the efficiency of crystal lattice packing.
  • The crystal structures determined provide insights into the intermolecular forces, including halogen bonding, that govern the solid-state behavior.
  • Significant parallels exist between the structural and melting point trends of dibromobenzene and dichlorobenzene isomers, suggesting general principles for halogenated aromatic compounds.